Sertraline hydrochloride, (1S-cis)-4-(3,4 dichlorophenl)-1,2,3,4-tetrahydro-N-methyl-1-naphthalenamine hydrochloride, having the formula 1 is approved, under the trademark Zoloft® by the US Food and Drug Administration, for the treatment of depression, obsessive-compulsive disorder and panic disorder.

U.S. Pat. No. 4,536,518 (“the “518 patent”) describes the preparation of sertraline hydrochloride with a melting point of 243-245° C. by treating an ethyl acetate/ether solution of the free base with gaseous hydrogen chloride. The solid state properties of the sertraline hydrochloride so produced are not otherwise disclosed.
U.S. Pat. No. 5,734,083 describes the preparation of a form of sertraline hydrochloride denominated polymorph “T1”.
According to U.S. Pat. No. 5,248,699 (“the “699 patent”), the sertraline hydrochloride produced by the method of the '518 patent has a crystalline form denominated “Form II” The '699 patent discloses four other polymorphs of sertraline hydrochloride designated Forms I, III, IV, and V, and characterizes them by single crystal x-ray analysis, powder x-ray diffraction, infra-red spectroscopy, and differential scanning calorimetry. The '699 patent reports that Form II is produced by rapid crystallization of sertraline hydrochloride from an organic solvent, including isopropyl alcohol, ethyl acetate or hexane, and generally describes methods for making sertraline hydrochloride Forms I-V. According to this patent, the preferential formation of Forms I, II or IV in an acidic solution consisting of isopropyl alcohol, hexane, acetone, methyl isobutyl ketone, glacial acetic acid or, preferably, ethyl acetate, depends on the rapidity of crystallization. The only method described in this patent for making Forms II and IV is by the rapid crystallization of sertraline hydrochloride from an organic solvent such as those listed above.
U.S. Pat. No. 6,452,054 describes novel polymorphic Forms XI, XII, XIII, XIV, XV and XVI of sertraline hydrochloride, processes for preparing them, methods of using them to treat disease, methods of using them to make other sertraline hydrochloride forms, and to pharmaceutical dosages containing the novel forms.
U.S. Pat. No. 6,495,721 discloses novel methods to make Form II of sertraline hydrochloride. Sertraline hydrochloride Form II may be produced directly from sertraline base or sertraline mandelate. It may also be produced from sertraline hydrochloride.
U.S. Pat. No. 6,500,987 is directed to Forms II, III, V, VI, VII, VIII, IX and X of sertraline hydrochloride and novel methods for their preparation.
U.S. Pat. No. 6,600,073 describes novel methods for the preparation of sertraline hydrochloride Forms III, V, VI, VII, VIII, IX and X.
United States Patent Application 0020183555 relates to a process for making sertraline hydrochloride Form II comprising the steps of dissolving sertraline base or sertraline mandelate in an organic solvent to form a solution, adding hydrogen chloride to the solution, heating the solution to a temperature between about room temperature and about reflux for a time sufficient to induce the formation of sertraline hydrochloride Form II; and isolating sertraline hydrochloride Form II.
US patent application 20030023117 describes new and novel polymorphic Forms XI, XII, XIII, XIV, XV and XVI of sertraline hydrochloride, processes for preparing and methods of using them to treat disease, methods of using them to make other sertraline hydrochloride Forms and to pharmaceutical dosages containing the novel forms.
US patent application 20030055112 describes Forms II, III, V, VI, VII, VIII IX and X of sertraline hydrochloride and novel methods for their preparation. According to the present invention, sertraline hydrochloride polymorph II may be produced by slurrying sertraline hydrochloride polymorph VI in an aprotic organic solvent. Sertraline hydrochloride polymorphic Form III may be produced by heating sertraline hydrochloride polymorphs V and VI. Sertraline hydrochloride Forms V and VI may be produced from either sertraline hydrochloride or sertraline base by crystallization. Sertraline hydrochloride Form VII may be produced by suspending sertraline chloride polymorph V in water, followed by filtration. Sertraline hydrochloride Forms VIII and IX may be produced by suspending sertraline base in water followed by acidification and filtration. Sertraline hydrochloride Form X may be produced by suspending sertraline hydrochloride in benzyl alcohol with heating, followed by filtration.
U.S. Pat. No. 6,517,866 deals with various salts of sertraline such as sertraline asparate, sertraline acetate, sertraline lactate and sustained release dosage forms thereof.